Journal
SYNTHESIS-STUTTGART
Volume 46, Issue 23, Pages 3233-3238Publisher
GEORG THIEME VERLAG KG
DOI: 10.1055/s-0034-1378997
Keywords
azlactones; quaternary amino acids; geminal bisphosphonates; Michael addition; biologically relevant molecules
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Funding
- National Center for Research and Development (NCBR) [LIDER/01/87/L3/11/NCBR/2012]
- Foundation for Polish Science
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Quaternary amino acids containing a geminal bisphosphonate moiety have been synthesized for the first time. The developed two-step reaction sequence utilizes the Michael addition of -substituted azlactones to a vinylidene bisphosphonate as the key step. The reaction proceeds under catalytic conditions with excellent regioselectivity. Subsequent, acid-mediated azlactone ring opening affords the target quaternary amino acids with good overall yields. Attempts to develop an enantioselective version of the synthetic strategy are described.
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